TDC 056: Storytelling, the most scalable post AI business skill worth building

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Jul 12, 2025

In a world inundated with AI content, the art of storytelling emerges as a vital skill for entrepreneurs. You’ll discover how stories resonate more deeply than mere information, creating lasting connections. The podcast highlights three essential storytelling types and unveils practical tips for capturing your audience's attention. Anecdotes, like a bear encounter and reflections on shared memories, underscore the importance of authentic narratives in navigating today’s fragmented media landscape. Embrace storytelling to stand out and engage!

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ANECDOTE

Bear In The Woods: Raw Vulnerability

Ryan describes a face-to-face encounter with a large black bear while wearing Crocs and socks and holding a crusty stick.
He uses the raw moment to illustrate vulnerability and the power of unprepared, authentic stories.

ANECDOTE

1:27 A.M. Keynote Panic

Ryan recounts waking at 1:27 a.m. in Cambridge with an unfinished keynote and his heart racing.
He links that messy moment to high engagement for his issue about being unprepared.

INSIGHT

Storytelling As The Scalable Post-AI Edge

Ryan argues storytelling is possibly the most scalable post-AI business skill because stories travel and stick.
He positions storytelling as the lever for connection in a fragmented, AI-saturated world.

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#056: Storytelling: The Most Scalable Post-AI Business Skill Worth Mastering

In a world of AI-generated content and fractured attention, your ability to tell compelling stories may be your greatest competitive advantage.

Episode Summary

In this episode of The Digital Contrarian, host Ryan Levesque dives into why storytelling is the most scalable post-AI business skill worth developing.

You'll learn how stories create deeper connection than any other content, discover the three story types you need to master, and find five contrarian tips for telling better stories that cut through the noise.

Question of the Day 🗣️

Where might you tell a story instead of simply dropping more content this week?

Key Take-aways

Stories travel and stick while other content gets forgotten quickly
While the best things in life don't scale, stories absolutely do
Three story types needed: first person (you), second person (someone you know), third person (out there)
Start with maximum tension, not context or setup
The parts you're tempted to skip are what audiences crave most

Timestamped Outline ⏱️

00:00 – The most scalable post-AI business skill
00:08 – Face-to-face with a bear (in crocs with socks)
01:13 – Why stories create deeper connection than any other content
03:51 – What 145 stories taught me about scale and connection
04:55 – The Winnie the Pooh effect: why stories scale across generations
09:30 – The power of shared stories as connective tissue
10:36 – Harari's insight: how stories built human civilization
13:00 – What makes a story captivating (not just nice)
18:19 – The three story types you need to master
24:44 – Five contrarian tips for telling better stories
28:18 – The one question to ask yourself this week

Links & Resources 🔗

Issue #023 of The Digital Contrarian – "The Secret Power of Being Unprepared" → https://ryanlevesque.net/the-power-of-being-unprepared/
Issue #054 of The Digital Contrarian – "The Breakdown of Shared Reality" → https://ryanlevesque.net/the-breakdown-of-shared-reality/
The Digital Contrarian newsletter → https://thedigitalcontrarian.com/

Next Steps & Subscribe 🚀

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